Compound and organic light emitting device using the same

ABSTRACT

The present invention provides a novel compound that is capable of largely improving lifespan, efficiency, electrochemical stability and thermal stability of the organic light emitting device, and an organic light emitting device in which the compound is included in an organic compound layer.

This application is a 35 U.S.C. §371 National Stage entry ofInternational Application No. PCT/KR2008/006564, filed on Nov. 7, 2008,and claims priority to Korean Application No. 10-2007-0113852, filed onNov. 8, 2007 and Korean Application No. 10-2008-0073238, filed on Jul.25, 2008, which are all hereby incorporated by reference in theirentireties.

TECHNICAL FIELD

The present invention relates to an organic light emitting device inwhich a novel compound that is capable of largely improving a life span,efficiency, electrochemical stability and thermal stability of theorganic light emitting device is included in an organic compound layer.This application claims priority from Korean Patent Application Nos.10-2007-0113852 and 10-2008-0073238 filed on Nov. 18, 2007 and Jul. 25,2008, in the KIPO, the disclosure of which is incorporated herein byreference in its entirety.

BACKGROUND ART

An organic light emission phenomenon is an example of a conversion ofcurrent into visible rays through an internal process of a specificorganic molecule. The organic light emission phenomenon is based on thefollowing mechanism. When organic material layers are interposed betweenan anode and a cathode, if voltage is applied between the twoelectrodes, electrons and holes are injected from the cathode and theanode into the organic material layer. The electrons and the holes whichare injected into the organic material layer are recombined to form anexciton, and the exciton is reduced to a bottom state to emit light. Anorganic light emitting device which is based on the above mechanismtypiccollectivelyy comprises a cathode, an anode, and organic materiallayer(s), for example, organic material layers including a holeinjection layer, a hole transport layer, a light emitting layer, and anelectron transport layer, interposed therebetween.

The materials used in the organic light emitting device are mostly pureorganic materials or complexes of organic material and metal. Thematerial used in the organic light emitting device may be classified asa hole injection material, a hole transport material, a light emittingmaterial, an electron transport material, or an electron injectionmaterial, according to its use. In connection with this, an organicmaterial having a p-type property, which is easily oxidized and iselectrochemiccollectivelyy stable when it is oxidized, is mostly used asthe hole injection material or the hole transport material. Meanwhile,an organic material having an n-type property, which is easily reducedand is electrochemiccollectivelyy stable when it is reduced, is used asthe electron injection material or the electron transport material. Asthe light emitting layer material, an organic material having bothp-type and n-type properties is preferable, which is stable when it isoxidized and when it is reduced. Also a material having high lightemission efficiency for conversion of the exciton into light when theexciton is formed is preferable.

In addition, it is preferable that the material used in the organiclight emitting device further have the following properties.

First, it is preferable that the material used in the organic lightemitting device have excellent thermal stability. The reason is thatjoule heat is generated by movement of electric charges in the organiclight emitting device. NPB, which has recently been used as the holetransport layer material, has a glass transition temperature of 100° C.or lower, thus it is difficult to apply to an organic light emittingdevice requiring a high current.

Second, in order to produce an organic light emitting device that iscapable of being actuated at low voltage and has high efficiency, holesand electrons which are injected into the organic light emitting devicemust be smoothly transported to a light emitting layer, and must not bereleased out of the light emitting layer. To achieve this, a materialused in the organic light emitting device must have a proper band gapand a proper HOMO or LUMO energy levels. A LUMO energy level ofPEDOT:PSS, which is currently used as a hole transport material of anorganic light emitting device produced using a solution coating method,is lower than that of an organic material used as a light emitting layermaterial, thus it is difficult to produce an organic light emittingdevice having high efficiency and a long lifespan.

Moreover, the material used in the organic light emitting device musthave excellent chemical stability, electric charge mobility, andinterfacial characteristic with an electrode or an adjacent layer. Thatis to say, the material used in the organic light emitting device mustbe little deformed by moisture or oxygen. Furthermore, proper hole orelectron mobility must be assured so as to balance densities of theholes and of the electrons in the light emitting layer of the organiclight emitting device to maximize the formation of excitons.Additionally, it has to be able to have a good interface with anelectrode including metal or metal oxides so as to assure stability ofthe device.

Accordingly, there is a need to develop an organic material having theabove-mentioned requirements in the art.

DISCLOSURE

Technical Problem

Therefore, the present inventors aim to provide an organic lightemitting device that includes a heterocompound derivative which iscapable of satisfying conditions required of a material which may beused for an organic light emitting device, for example, a proper energylevel, electrochemical stability, and thermal stability, and which has achemical structure capable of playing various roles required for theorganic light emitting device, depending on a substituent group.

Technical Solution

The present invention provides a compound of the following Formula 1.

In addition, the present invention provides an organic light emittingdevice which comprises a first electrode, organic material layer(s)having one or more layers and comprising a light emitting layer, and asecond electrode, wherein the first electrode, the organic materiallayer(s), and the second electrode form a layered structure and at leastone layer of the organic material layer(s) includes a compound of thefollowing Formula 1 or a compound of Formula 1 into which athermosetting or photo-crosslinkable functional group is introduced:

wherein X is selected from the group consisting of hydrogen; an alkylgroup, which is substituted or unsubstituted with one or moresubstituent groups selected from the group consisting of a halogengroup, an alkyl group, an alkenyl group, an alkoxy group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted arylalkylgroup, a substituted or unsubstituted arylalkenyl group, a substitutedor unsubstituted hetero ring group, a substituted or unsubstitutedcarbazolyl group, a substituted or unsubstituted fluorenyl group, anitrile group and an acetylene group; an alkoxy group, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkenyl group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an aryl group, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an hetero ring group including O, N or S as aheteroatom, which is substituted or unsubstituted with one or moresubstituent groups selected from the group consisting of a halogengroup, an alkyl group, an alkenyl group, an alkoxy group, a substitutedor unsubstituted arylamine group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a carbazolyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; —N(R′)(R″); a nitrile group; a nitro group; a halogengroup; —CO—N(R′)(R″); and —COO—R′,

R′ and R″ are each independently selected from the group consisting ofhydrogen, a halogen group, an alkyl group, an alkenyl group, an alkoxygroup, a substituted or unsubstituted aryl group, a substituted orunsubstituted arylalkyl group, a substituted or unsubstitutedarylalkenyl group, a substituted or unsubstituted hetero ring group, asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted fluorenyl group, a nitrile group and an acetylene group,

L is an arylene group having 6 to 40 carbon atoms, which is substitutedor unsubstituted with one or more substituent groups selected from thegroup consisting of nitro, nitrile, halogen, an alkyl group, an alkoxygroup and an amino group; a divalent hetero ring group, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of nitro, nitrile, halogen, an alkylgroup, an alkoxy group and an amino group; or a fluorenylene group,which is substituted or unsubstituted with one or more substituentgroups selected from the group consisting of nitro, nitrile, halogen, analkyl group, an alkoxy group and an amino group,

R₁ and R₂ are each independently selected from the group consisting ofhydrogen; deuterium; an alkyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkoxy group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an alkenyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an aryl group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an hetero ring groupincluding O, N or S as a heteroatom, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted arylamine group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; a carbazolyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an aryloxy group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an arylthio group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkoxycarbonyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a hydroxyl group; a carboxyl group; a nitrile group; anitro group; a halogen group; —N(R′)(R″); a nitrile group; a nitrogroup; a halogen group; —CO—N(R′)(R″); and —COO—R′, and said R₁ and R₂may form an aliphatic or hetero condensation ring in conjunction withadjacent groups, and

at least one of R₃ to R₉ is selected from the group consisting ofdeuterium; an alkenyl group, which is substituted or unsubstituted withone or more substituent groups selected from the group consisting of ahalogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an hetero ring groupincluding O, N or S as a heteroatom, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted arylamine group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; a carbazolyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted aryl alkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a nitrile group; —CO—N(R′)(R″); and —COO—R′, and saidR₃ to R₉ may form an aliphatic or hetero condensation ring inconjunction with adjacent groups, and the remains of R₃ to R₉ areselected from hydrogen or deuterium.

[Advantageous Effects]

A compound according to the present invention is configured so thatstability in respects to a hole and an electron is increased whileproperties of carbazole are not largely changed by introducing deuteriumto carbazole. These compounds may be used as an organic material layermaterial, particularly, a hole injection material and/or a holetransport material in an organic light emitting device, and in the caseof when it is used in the organic light emitting device, a drivingvoltage of the device may be reduced, light efficiency may be improved,and a life span property of the device may be improved.

DESCRIPTION OF DRAWINGS

FIG. 1 illustrates an organic light emitting device comprising asubstrate 1, an anode 2, a light emitting layer 3, and a cathode 4; and

FIG. 2 illustrates an organic light emitting device comprising asubstrate 1, an anode 2, a hole injection layer 5, a hole transportlayer 6, a light emitting layer 7, an electron transport layer 8, and acathode 4.

BEST MODE

A substituent group of Formula 1 will be described in detail below.

It is preferable that X of Formula 1 is selected from the groupconsisting of hydrogen; an alkyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkoxy group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an alkenyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an aryl group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an hetero ring groupincluding O, N or S as a heteroatom, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted arylamine group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; a carbazolyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; —N(R′)(R″); a nitrile group; a nitro group; a halogengroup; —CO—N(R′)(R″); and —COO—R′, and

it is preferable that R′ and R″ are each independently selected from thegroup consisting of hydrogen, a halogen group, an alkyl group, analkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group.

In addition, in the case of when X of Formula 1 is an aryl group, itmaybe selected from a monocyclic aromatic ring, such as a phenyl group,a biphenyl group, a terphenyl group, and a stilbene, and a multicyclicaromatic ring, such as a naphthyl group, an anthracenyl group, aphenanthrene group, a pyrenyl group, and a perylenyl group, and in thecase of when X is a hetero ring group, it may be selected from the groupconsisting of a thiophenyl group, a furan group, a pyrrolyl group, animidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolylgroup, a triazolyl group, a pyridyl group, a pyradazine group, aquinolinyl group, an isoquinoline group, and an acridyl group, and maybe selected from a carbazolyl group and a fluorenyl group, but notlimited thereto.

It is preferable that L of Formula 1 is an arylene group having 6 to 40carbon atoms, which is substituted or unsubstituted with one or moresubstituent groups selected from the group consisting of nitro, nitrile,halogen, an alkyl group, an alkoxy group and an amino group; a divalenthetero ring group, which is substituted or unsubstituted with one ormore substituent groups selected from the group consisting of nitro,nitrile, halogen, an alkyl group, an alkoxy group and an amino group; ora fluorenylene group, which is substituted or unsubstituted with one ormore substituent groups selected from the group consisting of nitro,nitrile, halogen, an alkyl group, an alkoxy group and an amino group.

In addition, it is more preferable that L is a phenylene group, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of nitro, nitrile, halogen, an alkylgroup, an alkoxy group and an amino group; a divalent hetero ring groupincluding O, N or S, and having 5 or 6 carbon atoms, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of nitro, nitrile, halogen, an alkylgroup, an alkoxy group and an amino group; or a fluorenylene group,which is substituted or unsubstituted with one or more substituentgroups selected from the group consisting of nitro, nitrile, halogen, analkyl group, an alkoxy group and an amino group, and it is mostpreferable that it is a phenylene group or a fluorenylene group.

R₁ and R₂ of Formula 1 are each independently selected from the groupconsisting of hydrogen; deuterium; an alkyl group, which is substitutedor unsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkoxy group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an alkenyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an aryl group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an hetero ring groupincluding O, N or S as a heteroatom, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted arylamine group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; a carbazolyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an aryloxy group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an arylthio group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkoxycarbonyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a hydroxyl group; a carboxyl group; a nitrile group; anitro group; a halogen group; —N(R′)(R″); a nitrile group; a nitrogroup; a halogen group; —CO—N(R′)(R″); and —COO—R′, and said R₁ and R₂may form an aliphatic or hetero condensation ring in conjunction withadjacent groups, and

it is preferable that at least one of R₃ to R₉ is selected from thegroup consisting of deuterium; an alkenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an hetero ring group including O, N or S as aheteroatom, which is substituted or unsubstituted with one or moresubstituent groups selected from the group consisting of a halogengroup, an alkyl group, an alkenyl group, an alkoxy group, a substitutedor unsubstituted arylamine group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a carbazolyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a nitrile group; —CO—N(R′)(R″); and COO—R′, and said R₃to R₉ may form an aliphatic or hetero condensation ring in conjunct ionwith adjacent groups, and the remains of R₃ to R₉ are selected fromhydrogen or deuterium.

In addition, it is more preferable that R₁ and R₂ are each independentlyan aryl group, which is substituted or unsubstituted with one or moresubstituent groups selected from the group consisting of a halogengroup, an alkyl group, an alkenyl group, an alkoxy group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted arylalkylgroup, a substituted or unsubstituted arylalkenyl group, a substitutedor unsubstituted hetero ring group, a substituted or unsubstitutedcarbazolyl group, a substituted or unsubstituted fluorenyl group, anitrile group and an acetylene group; or an hetero ring group includingO, N or S as a heteroatom, which is substituted or unsubstituted withone or more substituent groups selected from the group consisting of ahalogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted arylamine group, a substituted orunsubstituted aryl group, a substituted or unsubstituted arylalkylgroup, a substituted or unsubstituted arylalkenyl group, a substitutedor unsubstituted hetero ring group, a substituted or unsubstitutedcarbazolyl group, a substituted or unsubstituted fluorenyl group, anitrile group and an acetylene group.

In addition, it is most preferable that R₁ and R₂ are each independentlyany one of the following groups, but is not limited thereto.

In R₁ to R₉ of Formula 1, the number of carbon atoms of the alkyl group,the alkoxy group, and the alkenyl group is not particularly limited, butit is preferable that it is in the range of 1 to 20.

The length of the alkyl group that is included in the compound does notaffect the conjugation length of the compound, but may auxiliarilyaffect an application method of the compound to the organic lightemitting device, for example, the application of a vacuum depositionmethod or a solution coating method.

Illustrative, but non-limiting, examples of the aryl group of R₁ to R₉of Formula 1 include monocyclic aromatic rings, such as a phenyl group,a biphenyl group, a terphenyl group, and a stilbene group, andmulticyclic aromatic rings, such as a naphthyl group, an anthracenylgroup, a phenanthrene group, a pyrenyl group, and a perylenyl group.

Illustrative, but non-limiting, examples of the hetero ring group of R₁to R₉ of Formula 1 include a thiophenyl group, a furan group, a pyrrolylgroup, an imidazolyl group, a thiazolyl group, an oxazolyl group, anoxadiazolyl group, a triazolyl group, a pyridyl group, a pyradazinegroup, a quinolinyl group, an isoquinoline group, and an acridyl group.

Preferably, the compound of Formula 1 may be a compound that isrepresented by the following Formulas.

As shown in Formula 1, the compound of Formula 1 may have a propertythat is required when it is used as an organic material layer used in anorganic light emitting device by using a structure in which carbazole issubstituted with arylene and the like as a core structure andintroducing various substituents, particularly, deuterium.

The conjugation length of the compound has a close relationship with anenergy band gap. In detail, the energy band gap is reduced as theconjugation length of the compound increases. As described above, sincea conjugation structure is limited in the core structure of the compoundof Formula 1, the core structure has a large energy band gap.

As described above, in the present invention, various substituent groupsare introduced to R₁ to R₉ and X positions of the core structure havingthe large energy band gap so as to produce compounds having variousenergy band gaps. Generally, it is easy to control an energy band gap byintroducing substituent groups into a core structure having a largeenergy band gap, but it is difficult to significantly control the energyband gap by introducing substituent groups into a core structure havinga small energy band gap. Furthermore, in the present invention, it ispossible to control HOMO and LUMO energy levels of the compound byintroducing various substituent groups into R₁ to R₉ and X of the corestructure.

Additionally, by introducing various substituent groups into the corestructure, compounds having intrinsic characteristics of the substituentgroups may be obtained. For example, substituent groups, which arefrequently applied to hole injection layer material, hole transportlayer material, light emitting layer material, and electron transportlayer materials during the production of the organic light emittingdevice, are introduced into the core structure so as to producesubstances capable of satisfying the requirements of each organicmaterial layer.

Since the core structure of the compound of Formula 1 includes the aminestructure, it has an energy level suitable for the hole injection and/orhole transport materials in the organic light emitting device. In thepresent invention, the compound having the proper energy level isselected depending on the substituent group among the compoundsrepresented by Formula 1 to be used in the organic light emittingdevice, thereby it is possible to realize a device having a low drivingvoltage and a high light efficiency.

Furthermore, various substituent groups, in particular, hydrogen ordeuterium, are introduced into the core structure so as to preciselycontrol the energy band gap, and to improve interfacial characteristicswith organic materials, thereby apply the compound to various fields.

Meanwhile, since the compound of Formula 1 has a high glass transitiontemperature (Tg), it has excellent thermal stability. Such increase inthermal stability is an important factor providing driving stability tothe device.

Furthermore, the compound of Formula 1 may be used to form the organicmaterial layer using a vacuum deposition process or a solution coatingprocess during the production of the organic light emitting device. Inconnection with this, illustrative, but non-limiting, examples of thesolution coating process include a spin coating process, a dip coatingprocess, an inkjet printing process, a screen printing process, a sprayprocess, and a roll coating process.

The organic light emitting device of the present invention may beproduced using known materials through a known process, modified only inthat at least one layer of organic material layer(s) include thecompound of the present invention, that is, the compound of Formula 1.

The organic material layer(s) of the organic light emitting deviceaccording to the present invention may have a single layer structure, oralternatively, a multilayered structure in which at least two organicmaterial layers are layered. For example, the organic light emittingdevice of the present invention may comprise a hole injection layer, ahole transport layer, alight emitting layer, an electron transportlayer, and an electron injection layer as the organic material layer(s).However, the structure of the organic light emitting device is notlimited to this, but may comprise a smaller number of organic materiallayers.

Furthermore, the organic light emitting device of the present inventionmay be produced, for example, by sequentially layering a firstelectrode, organic material layer(s), and a second electrode on asubstrate. In connection with this, a physical vapor deposition (PVD)method, such as a sputtering method or an e-beam evaporation method, maybe used, but the method is not limited to these.

Mode for Invention

A better understanding of a method of manufacturing an compoundrepresented by Formula 1 and the manufacturing of an organic lightemitting device using the same may be obtained in light of the followingExamples which are set forth to illustrate, but are not to be construedto limit the present invention.

EXAMPLE 1 Manufacturing of the Compound Represented by Formula 2

EXAMPLE 1-1 Manufacturing of the Compound A

N-phenylcarbazole (27 g, 111 mmol) was dissolved in chloroform (200 mL),N-bromosuccinimide (39.5 g, 222 mmol) was added thereto, and they wereagitated for 5 hours at normal temperature. Distilled water was put intothe reaction solution and the organic layer was extracted. It was driedby using anhydrous magnesium sulfate, distilled under the reducedpressure, and recrystallized by using tetrahydrofuran and ethanol toobtain a compound A (39 g, yield 88%). MS: [M+H]⁺=401

EXAMPLE 1-2 Manufacturing of the Compound B

The compound A (30 g, 74.8 mmol) that was manufactured in Example 1-1was dissolved in anhydrous tetrahydrofuran (200 ml), n-butyl lithium(2.5M hexane solution, 36 ml, 89.8 mmol) was added dropwise at −78° C.,and after 1 hour, heavy water (2.24 g, 112 mmol) was put thereinto.After it was heated to normal temperature, water (50 ml) was putthereinto, it was agitated, and the organic layer was separated. Theorganic layer was dried by using anhydrous magnesium sulfate, filtered,and distilled under the reduced pressure. It was recrystallized by usinghexane to obtain a compound B (12 g, yield 50%). MS: [M+H]⁺=323

EXAMPLE 1-3 Manufacturing of the Compound C

After the compound B (12 g, 37.2 mmol) that was manufactured in Example1-2 and 4-chlorophenyl boronic acid (6.3 g, 40 mmol) were dissolved intetrahydrofuran (50 ml), tetrakis(triphenylphosphine)palladium (0.86 g,0.74 mmol) and 2N potassium carbonate aqueous solution were putthereinto and refluxed for 12 hours. After the reaction was finished, itwas cooled to normal temperature, and the organic layer was separatedand dried by using anhydrous magnesium sulfate. After it was distilledunder the reduced pressure, it was recrystallized by using ethanol toobtain a compound C (11 g, yield 84%). MS: [M+H]⁺=354

EXAMPLE 1-4 Manufacturing of the Compound 2

The compound C (4 g, 11.3 mmol) that was manufactured in Example 1-3 andbis(4-biphenylyl)amine (4.18 g, 13 mmol) were dissolved in xylene (100ml), sodium-tertiary-butoxide (1.4 g, 14.7 mmol) and bis(tritertiary-butyl phosphine)palladium (0.11 g, 0.23 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature, anacidic white clay was put, and then agitated. After it was filtered, itwas distilled under the reduced pressure and subjected to columnpurification by using a hexane/tetrahydrofuran=10/1 solvent to obtainFormula 2 (3.9 g, yield 54%). MS: [M+H]⁺=639

EXAMPLE 2 Manufacturing of the Compound Represented by Formula 3

EXAMPLE 2-1 Manufacturing of the Compound A

Carbazole (20 g, 119.6 mmol) and 4-bromobiphenyl (28 g, 120 mmol) weredissolved in xylene (400 ml), sodium-tertiary-butoxide (15 g, 156 mmol)and bis (tri tertiary-butyl phosphine)palladium (0.6 g, 1.2 mmol) wereadded thereto, and they were refluxed for 12 hours under a nitrogenatmosphere. After the reaction was finished, it was cooled to normaltemperature, and the manufactured solid was filtered. It wassequentially washed by using toluene and ethanol, and dried to obtain acompound A (31.8 g, yield 83%). MS: [M+H]⁺=320

EXAMPLE 2-2 Manufacturing of the Compound B

The compound A (30 g, 93.9 mmol) that was manufactured in Example 2-1was dissolved in chloroform (500 mL), N-bromosuccinimide (35.6 g, 200mmol) was added thereto, and they were agitated for 5 hours at normaltemperature. Distilled water was put into the reaction solution and theorganic layer was extracted. It was distilled under the reducedpressure, and recrystallized by using tetrahydrofuran and ethanol toobtain a compound B (39.4 g, yield 88%). MS: [M+H]⁺=478

EXAMPLE 2-3 Manufacturing of the Compound C

The compound B (35 g, 73.3 mmol) that was manufactured in Example 2-2was dissolved in anhydrous tetrahydrofuran (500 ml), n-butyl lithium(2.5M hexane solution, 29.3 ml, 73.3 mmol) was added dropwise at −78°C., and after 1 hour, heavy water (2.24 g, 112 mmol) was put thereinto.After it was heated to normal temperature, water (50 ml) was putthereinto, it was agitated, and the organic layer was separated. Theorganic layer was dried by using anhydrous magnesium sulfate, filtered,and distilled under the reduced pressure. It was recrystallized by usinghexane to obtain a compound C (14 g, yield 48%). MS. [M+H]⁺=400

EXAMPLE 2-4 Manufacturing of the Compound D

After the compound C (14 g, 35 mmol) that was manufactured in Example2-3 and 4-chlorophenyl boronic acid (5.9 g, 38 mmol) were dissolved intetrahydrofuran (150 ml), tetrakis(triphenylphosphine)palladium (0.81 g,0.7 mmol) and 2N potassium carbonate aqueous solution were put thereintoand refluxed for 12 hours. After the reaction was finished, it wascooled to normal temperature, and the manufactured solid was filtered.It was sequentially washed by using water and ethanol and dried toobtain a compound D (12.8 g, yield 85%)). MS: [M+H]⁺=431

EXAMPLE 2-5 Manufacturing of the Formula 3

The compound D (10 g, 23.2 mmol) that was manufactured in Example 2-4and bis(4-biphenylyl)amine (7.7 g, 24 mmol) were dissolved in xylene inan amount of 100 ml, sodium-tertiary-butoxide (2.9 g, 30 mmol) andbis(tri tertiary-butyl phosphine)palladium (0.11 g, 0.23 mmol) wereadded thereto, and they were refluxed for 5 hours under a nitrogenatmosphere. After the reaction was finished, it was cooled to normaltemperature, and the manufactured solid was filtered. It wassequentially washed by using toluene and ethanol, dissolved inchloroform, an acidic white clay was put thereinto, and they wereagitated. After it was filtered, distilled under the reduced pressure,and recrystallized by using tetrahydrofuran and ethanol to obtainFormula 3 (10.1 g, yield 61%). MS: [M+H]⁺=716

EXAMPLE 3 Manufacturing of the Compound Represented by Formula 4

EXAMPLE 3-1 Manufacturing of the Compound A

After 2-bromothiopene (20 g, 122.7 mmol) and phenyl boronate (15.9 g,130.4 mmol) were dissolved in tetrahydrofuran (150 ml),tetrakis(triphenylphosphine)palladium (2.9 g, 2.5 mmol) and 2N potassiumcarbonate aqueous solution were put thereinto and refluxed for 12 hours.After the reaction was finished, it was cooled to normal temperature,and the organic layer was separated and dried by using anhydrousmagnesium sulfate. After it was distilled under the reduced pressure, itwas recrystallized by using hexane at 0° C. to obtain a compound A (17.2g, yield 87%). MS: [M+H]⁺=161

EXAMPLE 3-2 Manufacturing of the Compound B

The compound A (15 g, 93.6 mmol) that was manufactured in Example 3-1was dissolved in anhydrous tetrahydrofuran (300 ml), n-butyl lithium(2.5M hexane solution, 41.2 ml, 103 mmol) was added dropwise at −78° C.,and after 1 hour, trimethyl borate (11. 4 g, 110 mmol) was putthereinto. After 1 hour, 1N hydrogen chloride aqueous solution was putthereinto, and it was heated to normal temperature. After the organiclayer was separated, it was dried by using anhydrous magnesium sulfate,and distilled under the reduced pressure. It was recrystallized by usingethyl ether and hexane to obtain a compound B (13 g, yield 68%). MS:[M+H]⁺=205

EXAMPLE 3-3 Manufacturing of the Compound C

After the compound B (13 g, 63.7 mmol) that was manufactured in Example3-2 and 1-bromo-3-iodobenzene (19.8 g, 70 mmol) were dissolved intetrahydrofuran (200 ml), tetrakis(triphenylphosphine)palladium (1.5 g,1.3 mmol) and 2N potassium carbonate aqueous solution were put thereintoand refluxed for 12 hours. After the reaction was finished, it wascooled to normal temperature, and the organic layer was separated anddried by using anhydrous magnesium sulfate. After it was distilled underthe reduced pressure, it was recrystallized by using tetrahydrofuran andethanol to obtain a compound C (14.8 g, yield 74%). MS: [M+H]⁺=316

EXAMPLE 3-4 Manufacturing of the Compound D

Carbazole (5 g, 29.9 mmol) and the compound C (9.4 g, 29.9 mmol) thatwas manufactured in Example 3-3 were suspended in xylene (100 ml),sodium-tertiary-butoxide (3.7 g, 38 mmol) and bis (tri tertiary-butylphosphine)palladium (0.15 g, 0.3 mmol) were added thereto, and they wererefluxed for 12 hours under a nitrogen atmosphere. After the reactionwas finished, it was cooled to normal temperature, and the manufacturedsolid was filtered. It was sequentially washed by using toluene andethanol, and dried to obtain a compound D (9.5 g, yield 79%). MS:[M+H]⁺=402

EXAMPLE 3-5 Manufacturing of the Compound E

The compound D (9 g, 22.4 mmol) that was manufactured in Example 3-4 wasdissolved in chloroform (100 mL), N-bromosuccinimide (8 g, 45 mmol) wasadded thereto, and they were agitated for 5 hours at normal temperature.Distilled water was put into the reaction solution and the organic layerwas extracted. It was distilled under the reduced pressure, andrecrystallized by using tetrahydrofuran and ethanol to obtain a compoundE (11.2 g, yield 89%). MS: [M+H]⁺=560

EXAMPLE 3-6 Manufacturing of the Compound F

The compound E (11 g, 19.7 mmol) that was manufactured in Example 3-5was dissolved in anhydrous tetrahydrofuran (200 ml), n-butyl lithium(2.5M hexane solution, 7.9 ml, 19.7 mmol) was added dropwise at −78° C.,and after 1 hour, heavy water (0.6 g, 30 mmol) was put thereinto. Afterit was heated to normal temperature, water (50 ml) was put thereinto, itwas agitated, and the organic layer was separated. The organic layer wasdried by using anhydrous magnesium sulfate, filtered, and distilledunder the reduced pressure. It was recrystallized by usingtetrahydrofuran and ethanol to obtain a compound F (4.9 g, yield 52%).MS: [M+H]⁺=482

EXAMPLE 3-7 Manufacturing of the Compound G

After the compound F (4.5 g, 9.3 mmol) that was manufactured in Example3-6 and 4-chlorophenyl boronic acid (1.7 g, 11 mmol) were dissolved intetrahydrofuran (100 ml), tetrakis(triphenylphosphine)palladium (0.22 g,0.19 mmol) and 2N potassium carbonate aqueous solution were putthereinto and refluxed for 12 hours. After the reaction was finished, itwas cooled to normal temperature, and the organic layer was separatedand dried by using anhydrous magnesium sulfate and filtered. After itwas distilled under the reduced pressure, it was recrystallized by usingtetrahydrofuran and ethanol to obtain a compound G (3.8 g, yield 79%).MS: [M+H]⁺=513

EXAMPLE 3-8 Manufacturing of the Formula 4

The compound G(3.5 g, 6.8 mmol) that was manufactured in Example 3-7 andN-phenyl-1-naphthyl amine (1.6 g, 7.3 mmol) were dissolved in xylene (80ml), sodium-tertiary-butoxide (0.85 g, 8.8 mmol) and bis(tritertiary-butyl phosphine)palladium (0.04 g, 0.08 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature,and an acidic white clay was put thereinto, and they were agitated.After it was filtered, distilled under the reduced pressure, andsubjected to the column purification by using ahexane/tetrahydrofuran=7/1 solvent and ethanol to obtain Formula 4 (2.9g, yield 61%). MS: [M+H]⁺=696

EXAMPLE 4 Manufacturing of the Compound Represented by Formula 7

EXAMPLE 4-1 Manufacturing of the Compound A

The compound C (5 g, 14.1 mmol) that was manufactured in Example 1-3 and1-aminonaphthalene (2 g, 14 mmol) were dissolved in toluene (80 ml),sodium-tertiary-butoxide (1.7 g, 18 mmol) and bis(tri tertiary-butylphosphine)palladium (0.07 g, 0.14 mmol) were added thereto, and theywere refluxed for 5 hours under a nitrogen atmosphere. After thereaction was finished, it was cooled to normal temperature, and anacidic white clay was put thereinto, and they were agitated. After itwas filtered, distilled under the reduced pressure, and subjected to thecolumn purification by using a hexane/tetrahydrofuran=10/1 solvent andethanol to obtain a compound A (2.9 g, yield 61%). MS: [M+H]⁺=462

EXAMPLE 4-2 Manufacturing of the Formula 7

The compound A (2.5 g, 5.4 mmol) that was manufactured in Example 4-1and 2-bromo-9, 9-dimethylfluorene (1.6 g, 5.9 mmol) were dissolved intoluene (80 ml), sodium-tertiary-butoxide (0.67 g, 7 mmol) and bis(tritertiary-butyl phosphine)palladium (0.03 g, 0.06 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature,and an acidic white clay was put thereinto, and they were agitated.After it was filtered, distilled under the reduced pressure, andsubjected to the column purification by using ahexane/tetrahydrofuran=8/1 solvent to obtain a compound 7 (2.1 g, yield59%). MS: [M+H]⁺=654

EXAMPLE 5 Manufacturing of the Compound Represented by Formula 13

EXAMPLE 5-1 Manufacturing of the Compound A

Into the solution in which a nitric acid (40 ml) and an acetic acid (40ml) were mixed with each other, 4,4′-dibromobiphenyl (18 g, 57.7 mmol)was slowly put while it was suspended in dichloromethane (50 ml) and anacetic acid (300 ml). After 18 hours, the reaction solution was pouredinto the sodium hydroxide aqueous solution to neutralize it, and it wasextracted by using dichloromethane. The organic layer was dried by usinganhydrous magnesium sulfate and distilled under the reduced pressure,recrystallized by using methanol to obtain a compound A (16.9 g, yield82%). MS: [M+H]+=358

EXAMPLE 5-2 Manufacturing of the Compound B

The compound A (16 g, 44.8 mmol) that was manufactured in Example 5-1and triphenyl phosphine (29.4 g, 112 mmol) were mixed with each other,and it was refluxed while o-dichlorobenzene (100 ml) was put thereintoand agitated. After the reaction was finished, it was cooled to normaltemperature and distilled under the reduced pressure. It was subjectedto the column purification by using a ligroin/dichloromethane=3/1solvent to obtain a compound B (10.6 g, yield 73%). MS: [M+H]⁺=326

EXAMPLE 5-3 Manufacturing of the Compound C

The compound B(10 g, 30.7 mmol) that was manufactured in Example 5-2 andiodobiphenyl (11.2 g, 40 mmol), and potassium carbonate (8.3 g, 60 mmol)were suspended in dimethylacetamide (100 ml), copper (2 g, 31.5 mmol)was put thereinto, and they were refluxed for 12 hours under a nitrogenatmosphere. After the reaction was finished, it was cooled to normaltemperature, and was filtered. The filtration solution was poured intowater, extracted by using chloroform, and dried by using anhydrousmagnesium sulfate. After it was distilled under the reduced pressure, itwas subjected to the column purification by using ahexane/tetrahydrofuran=10/1 solvent to obtain a compound C (6.2 g, yield42%). MS: [M+H]⁺=478

EXAMPLE 5-4 Manufacturing of the Compound D

The compound C (6 g, 12.6 mmol) that was manufactured in Example 5-3 wasdissolved in anhydrous tetrahydrofuran (100 ml), n-butyl lithium (2.5Mhexane solution, 12.1 ml, 30.2 mmol) was added dropwise at −78° C., andafter 1 hour, heavy water (1.1 g, 55 mmol) was put thereinto. After itwas heated to normal temperature, water (30 ml) was put thereinto, itwas agitated, and the organic layer was separated. The organic layer wasdried by using anhydrous magnesium sulfate, filtered, and distilledunder the reduced pressure. It was recrystallized by usingtetrahydrofuran and ethanol to obtain a compound D (2.4 g, yield 59%).MS: [M+H]⁺=322

EXAMPLE 5-5 Manufacturing of the Compound E

The compound D (2 g, 6.2 mmol) that was manufactured in Example 5-4 wasdissolved in chloroform (60 mL), N-bromosuccinimide (1.1 g, 6.2 mmol)was added thereto, and they were agitated for 5 hours at normaltemperature. Distilled water was put into the reaction solution and theorganic layer was extracted. It was distilled under the reducedpressure, and recrystallized by using tetrahydrofuran and ethanol toobtain a compound E (1.8 g, yield 73%). MS: [M+H]⁺=401

EXAMPLE 5-6 Manufacturing of the Compound F

After the compound E (1.5 g, 3.7 mmol) that was manufactured in Example5-5 and 4-chlorophenyl boronic acid (0.69 g, 4.4 mmol) were dissolved intetrahydrofuran (70 ml), tetrakis(triphenylphosphine)palladium (0.09 g,0.07 mmol) and 2N potassium carbonate aqueous solution were putthereinto and refluxed for 12 hours. After the reaction was finished, itwas cooled to normal temperature, and the organic layer was separatedand dried by using anhydrous magnesium sulfate. After it was distilledunder the reduced pressure, it was recrystallized by usingtetrahydrofuran and ethanol to obtain a compound F (1.1 g, yield 69%).MS: [M+H]⁺=432

EXAMPLE 5-7 Manufacturing of the Formula 13

The compound F (1.1 g, 2.5 mmol) that was manufactured in Example 5-6and bis(4-biphenylyl)amine (0.87 g, 2.7 mmol) were dissolved in xylene(50 ml), sodium-tertiary-butoxide (0.32 g, 3.3 mmol) and bis(tritertiary-butyl phosphine)palladium (0.02 g, 0.04 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature, anacidic white clay was put, and then agitated. After it was filtered, itwas distilled under the reduced pressure and recrystallized by usingtetrahydrofuran and ethanol to obtain Formula 13 (1.1 g, yield 61%). MS:[M+H]⁺=717

EXAMPLE 6 Manufacturing of the Compound Represented by Formula 17

EXAMPLE 6-1 Manufacturing of the Compound A

The compound F (2 g, 4.6 mmol) that was manufactured in Example 5-6 andp-toluydine (0.59 g, 5.5 mmol) were dissolved in xylene (50 ml),sodium-tertiary-butoxide (0.58 g, 6 mmol) and bis(tri tertiary-butylphosphine)palladium (0.02 g, 0.04 mmol) were added thereto, and theywere refluxed for 5 hours under a nitrogen atmosphere. After thereaction was finished, it was cooled to normal temperature, an acidicwhite clay was put, and then agitated. After it was filtered, it wasdistilled under the reduced pressure and subjected to columnpurification by using a hexane/tetrahydrofuran=8/1 solvent to obtain thecompound A (1.6 g, yield 69%). MS: [M+H]⁺=503

EXAMPLE 6-2 Manufacturing of the Formula 17

The compound A (1.5 g, 3 mmol) that was manufactured in Example 6-1 and2-bromo-9,9-dimethylfluorene (0.9 g, 3.3 mmol) were dissolved in xylene(50 ml), sodium-tertiary-butoxide (0.37 g, 3.9 mmol) and bis(tritertiary-butyl phosphine)palladium (0.02 g, 0.04 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature, anacidic white clay was put, and then agitated. After it was filtered, itwas distilled under the reduced pressure and subjected to columnpurification by using a hexane/tetrahydrofuran=6/1 solvent to obtainFormula 17 (1.2 g, yield 58%). MS: [M+H]⁺=695

EXAMPLE 7 Manufacturing of the Compound Represented by Formula 22

EXAMPLE 7-1 Manufacturing of the Compound A

The compound B (10 g, 30.7 mmol) that was manufactured in Example 5-2,iodo benzene (8.2 g, 40 mmol), and potassium carbonate (8.3 g, 60 mmol)were suspended in dimethylacetamide (100 ml), copper (2 g, 31.5 mmol)was put thereinto, and they were refluxed for 12 hours under a nitrogenatmosphere. After the reaction was finished, it was cooled to normaltemperature, and was filtered. The filtration solution was poured intowater, extracted by using chloroform, and dried by using anhydrousmagnesium sulfate. After it was distilled under the reduced pressure, itwas subjected to the column purification by using ahexane/tetrahydrofuran=12/1 solvent to obtain a compound A (6.8 g, yield55%). MS: [M+H]⁺=402

EXAMPLE 7-2 Manufacturing of the Compound B

The compound A (6 g, 15 mmol) that was manufactured in Example 7-1 wasdissolved in anhydrous tetrahydrofuran (100 ml), n-butyl lithium (2.5Mhexane solution, 13.2 ml, 33 mmol) was added dropwise at −78° C., andafter 1 hour, heavy water (1.2 g, 60 mmol) was put thereinto. After itwas heated to normal temperature, water (30 ml) was put thereinto, itwas agitated, and the organic layer was separated. The organic layer wasdried by using anhydrous magnesium sulfate, filtered, and distilledunder the reduced pressure. It was recrystallized by using ethanol toobtain a compound E (2.6 g, yield 71%). MS: [M+H]⁺=246

EXAMPLE 7-3 Manufacturing of the Compound C

The compound B (2.5 g, 10.2 mmol) that was manufactured in Example 7-2was dissolved in chloroform (60 mL), N-bromosuccinimide (3.9 g, 22 mmol)was added thereto, and they were agitated for 5 hours at normaltemperature. Distilled water was put into the reaction solution and theorganic layer was extracted. It was distilled under the reducedpressure, and recrystallized by using tetrahydrofuran and ethanol toobtain a compound C (3.7 g, yield 90%). MS: [M+H]⁺=404

EXAMPLE 7-4 Manufacturing of the Compound D

The compound C (3.5 g, 8.7 mmol) that was manufactured in Example 7-3was dissolved in anhydrous tetrahydrofuran (80 ml), n-butyl lithium(2.5M hexane solution, 3.5 ml, 8.7 mmol) was added dropwise at −78° C.,and after 1 hour, heavy water (0.4 g, 20 mmol) was put thereinto. Afterit was heated to normal temperature, water (20 ml) was put thereinto, itwas agitated, and the organic layer was separated. The organic layer wasdried by using anhydrous magnesium sulfate, filtered, and distilledunder the reduced pressure. It was recrystallized by using hexane toobtain a compound D (1.3 g, yield 46%). MS: [M+H]⁺=326

EXAMPLE 7-5 Manufacturing of the Compound E

After the compound D (1.2 g, 3.7 mmol) that was manufactured in Example7-4 and 4-chlorophenyl boronic acid (0.69 g, 4.4 mmol) were dissolved intetrahydrofuran (70 ml), tetrakis(triphenylphosphine)palladium (0.09 g,0.07 mmol) and 2N potassium carbonate aqueous solution were putthereinto and refluxed for 12 hours. After the reaction was finished, itwas cooled to normal temperature, and the organic layer was separatedand dried by using anhydrous magnesium sulfate. After it was distilledunder the reduced pressure, it was recrystallized by usingtetrahydrofuran and ethanol to obtain a compound F (0.95 g, yield 72%).MS: [M+H]⁺=357

EXAMPLE 7-6 Manufacturing of the Formula 22

The compound E (0.9 g, 2.5 mmol) that was manufactured in Example 7-5and bis(4-biphenylyl)amine (0.87 g, 2.7 mmol) were dissolved in xylene(50 ml), sodium-tertiary-butoxide (0.32 g, 3.3 mmol) and bis(tritertiary-butyl phosphine)palladium (0.02 g, 0.04 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature, anacidic white clay was put, and then agitated. After it was filtered, itwas distilled under the reduced pressure and recrystallized by usingtetrahydrofuran and ethanol to obtain Formula 22 (1.2 g, yield 75%). MS:[M+H]⁺=642

EXAMPLE 8 Manufacturing of the Compound Represented by Formula 27

EXAMPLE 8-1 Manufacturing of the Compound A

The compound D (5 g, 15.6 mmol) that was manufactured in Example 5-4 wasdissolved in chloroform (80 mL), N-bromosuccinimide (5.7 g, 32 mmol) wasadded thereto, and they were agitated for 5 hours at normal temperatureAfter the reaction was finished, the manufactured solid was filtered. Itwas sequentially washed by using water and ethanol, and dried to obtaina compound A (6.8 g, yield 91%). MS: [M+H]⁺=480

EXAMPLE 8-2 Manufacturing of the Compound B

The compound A (6.5 g, 13.6 mmol) that was manufactured in Example 8-1was dissolved in anhydrous tetrahydrofuran (100 ml), n-butyl lithium(2.5M hexane solution, 5.4 ml, 13.6 mmol) was added dropwise at −78° C.,and after 1 hour, heavy water (0.5 g, 25 mmol) was put thereinto. Afterit was heated to normal temperature, water (20 ml) was put thereinto, itwas agitated, and the organic layer was separated. The organic layer wasdried by using anhydrous magnesium sulfate, filtered, and distilledunder the reduced pressure. It was recrystallized by usingtetrahydrofuran and ethanol to obtain a compound B (2.9 g, yield 53%).MS: [M+H]⁺=402

EXAMPLE 8-3 Manufacturing of the Compound C

After the compound B (2.5 g, 6.2 mmol) that was manufactured in Example8-2 and 4-chlorophenyl boronic acid (1.1 g, 7 mmol) were dissolved intetrahydrofuran (70 ml), tetrakis(triphenylphosphine)palladium (0.09 g,0.07 mmol) and 2N potassium carbonate aqueous solution were putthereinto and refluxed for 12 hours. After the reaction was finished, itwas cooled to normal temperature, and the organic layer was separatedand dried by using anhydrous magnesium sulfate. After it was distilledunder the reduced pressure, it was recrystallized by usingtetrahydrofuran and ethanol to obtain a compound C (2.1 g, yield 78%).MS: [M+H]⁺=433

EXAMPLE 8-4 Manufacturing of the Compound D

The compound C (2 g, 4.6 mmol) that was manufactured in Example 8-3 andaniline (0.51 g, 5.5 mmol) were dissolved in xylene (60 ml),sodium-tertiary-butoxide (0.58 g, 6 mmol) and bis(tri tertiary-butylphosphine)palladium (0.03 g, 0.06 mmol) were added thereto, and theywere refluxed for 5 hours under a nitrogen atmosphere. After thereaction was finished, it was cooled to normal temperature, an acidicwhite clay was put, and then agitated. After it was filtered, it wasdistilled under the reduced pressure and subjected to columnpurification by using a hexane/tetrahydrofuran=7/1 solvent to obtain thecompound D (1.6 g, yield 71%). MS: [M+H]⁺=490

EXAMPLE 8-5 Manufacturing of Formula 27

The compound D (1.5 g, 3.1 mmol) that was manufactured in Example 8-4and 3-bromo-N-phenylcarbazole (1 g, 3.1 mmol) were dissolved in xylene(60 ml), sodium-tertiary-butoxide (0.38 g, 4 mmol) and bis(tritertiary-butyl phosphine)palladium (0.02 g, 0.04 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature, anacidic white clay was put, and then agitated. After it was filtered, itwas distilled under the reduced pressure and subjected to columnpurification by using a hexane/tetrahydrofuran=6/1 solvent to obtainFormula 27 (1.5 g, yield 66%). MS: [M+H]⁺=731

EXAMPLE 9 Manufacturing of the Compound represented by Formula 32

EXAMPLE 9-1 Manufacturing of the Compound A

Into the solution in which a nitric acid (50 ml) and an acetic acid (50ml) were mixed with each other, 4,4′-dibromobiphenyl-D8 (20 g, 62.4mmol) was slowly put while it was suspended in dichloromethane (60 ml)and an acetic acid (400 ml). After 18 hours, the reaction solution waspoured into the sodium hydroxide aqueous solution to neutralize it, andit was extracted by using dichloromethane. The organic layer was driedby using anhydrous magnesium sulfate and distilled under the reducedpressure, recrystallized by using methanol to obtain a compound A (17.5g, yield 77%). MS: [M+H]+=365

EXAMPLE 9-2 Manufacturing of the Compound B

The compound A (17 g, 46.7 mmol) that was manufactured in Example 9-1and triphenyl phosphine (30.6 g, 116.8 mmol) were mixed with each other,and it was refluxed while o-dichlorobenzene (130 ml) was put thereintoand agitated. After the reaction was finished, it was cooled to normaltemperature and distilled under the reduced pressure. It was subjectedto the column purification by using a ligroin/dichloromethane=3/1solvent to obtain a compound B (10.9 g, yield 71%). MS: [M+H]⁺=332

EXAMPLE 9-3 Manufacturing of the Compound C

The compound B(10 g, 30.7 mmol) that was manufactured in Example 9-2,iodo benzene(7.3 g, 36 mmol), potassium carbonate(8.3 g, 60 mmol) weresuspended in dimethyl acetamide (100 ml), copper (2 g, 31.5 mmol) wasput thereinto, and they were refluxed for 12 hours under a nitrogenatmosphere. After the reaction was finished, it was cooled to normaltemperature, and was filtered. The filtration solution was poured intowater, extracted by using chloroform, and dried by using anhydrousmagnesium sulfate. After it was distilled under the reduced pressure, itwas subjected to the column purification by using ahexane/tetrahydrofuran=10/1 solvent to obtain a compound C (6.1 g, yield50%). MS: [M+H]⁺=408

EXAMPLE 9-4 Manufacturing of the Compound D

The compound C (6 g, 14.7 mmol) that was manufactured in Example 9-3 wasdissolved in anhydrous tetrahydrofuran (120 ml), n-butyl lithium (2.5Mhexane solution, 12.9 ml, 32.3 mmol) was added dropwise at −78° C., andafter 1 hour, heavy water (1.2 g, 60 mmol) was put thereinto. After itwas heated to normal temperature, water (30 ml) was put thereinto, itwas agitated, and the organic layer was separated. The organic layer wasdried by using anhydrous magnesium sulfate, filtered, and distilledunder the reduced pressure. It was recrystallized by using and ethanolto obtain a compound D (2.3 g, yield 62%). MS: [M+H]⁺=252

EXAMPLE 9-5 Manufacturing of the Compound E

The compound D (2 g, 8 mmol) that was manufactured in Example 9-4 wasdissolved in chloroform (60 mL), N-bromosuccinimide (1.4 g, 8 mmol) wasadded thereto, and they were agitated for 5 hours at normal temperature.Distilled water was put into the reaction solution and the organic layerwas extracted. It was distilled under the reduced pressure, and the nextreaction was performed without the purification process.

EXAMPLE 9-6 Manufacturing of the Compound F

After the compound E that was manufactured in Example 9-5 and4-chlorophenyl boronic acid (1.5 g, 9.6 mmol) were dissolved intetrahydrofuran (80 ml), tetrakis(triphenylphosphine)palladium (0.18 g,0.16 mmol) and 2N potassium carbonate aqueous solution were putthereinto and refluxed for 12 hours. After the reaction was finished, itwas cooled to normal temperature, and the organic layer was separatedand dried by using anhydrous magnesium sulfate. After it was distilledunder the reduced pressure, it was subjected to the column purificationby using a hexane/tetrahydrofuran=12/1 solvent to obtain a compound F(1.1 g, yield 39%). MS: [M+H]⁺=361

EXAMPLE 9-7 Manufacturing of Formula 32

The compound F (1 g, 2.8 mmol) that was manufactured in Example 9-6 andbis(4-biphenylyl)amine (0.9 g, 2.8 mmol) were dissolved in xylene (50ml), sodium-tertiary-butoxide (0.35 g, 3.6 mmol) and bis(tritertiary-butyl phosphine)palladium (0.02 g, 0.04 mmol) were addedthereto, and they were refluxed for 5 hours under a nitrogen atmosphere.After the reaction was finished, it was cooled to normal temperature, anacidic white clay was put, and then agitated. After it was filtered, itwas distilled under the reduced pressure and recrystallized by usingtetrahydrofuran and ethanol to obtain Formula 32 (1.2 g, yield 66%). MS:[M+H]⁺=646

EXPERIMENTAL EXAMPLE 1

A glass substrate, on which ITO (indium tin oxide) was applied to athickness of 1500 Å to form a thin film, was put in distilled water, inwhich a detergent was dissolved, and washed using ultrasonic waves. Inconnection with this, a product manufactured by Fischer Inc. was used asthe detergent, and distilled water was produced by filtering twice usinga filter manufactured by Millipore Inc. After ITO was washed for 30 min,ultrasonic washing was conducted twice using distilled water for 10 min.After the washing using distilled water was completed, ultrasonicwashing was conducted using isopropyl alcohol, acetone, and methanolsolvents, and drying was then conducted. Next, it was transported to aplasma washing machine. In addition, the substrate was washed usingoxygen plasma for 5 min, and then transported to a vacuum evaporator.

Hexanitrile hexaazatriphenylene (hereinafter, referred to as “HAT”) ofthe following Formula was vacuum deposited to a thickness of 500 Å byheating on a transparent ITO electrode, which was prepared through theabove procedure, so as to form a hole injection layer.

The compound of Formula 2, which was prepared in Example 1, was vacuumdeposited to a thickness of 400 Å by heating on the hole injection layerso as to form a hole transport layer.

Subsequently, on the hole transport layer, GH and GD as described belowwere vacuum deposited to a film thickness of 300 Å at a film thicknessratio of 20:1 so as to form a light emitting layer.

On the light emitting layer, the electron transport material asdescribed below was vacuum deposited to a thickness of 200 Å so as toform an electron injection layer and a electron transport layer.

[Electron Transport Material]

Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having athickness of 2000 Å were sequentially deposited on the electroninjection layer and the electron transport layer to form a cathode.

In the above procedure, the deposition speed of an organic material wasmaintained at 0.4 to 0.7 Å/sec, lithium fluoride and aluminum weredeposited at speeds of 0.3 Å/sec and 2 Å/sec, respectively, on thecathode, and in the deposition, a vacuum was maintained at 2×10⁻⁷ to5×10⁻⁸ torr.

A forward current density of 4.6 V was applied to the organic lightemitting device manufactured in the above, and as a result, the greenlight in which the color coordinate was (0.32, 0.65) at a currentdensity of 50 mA/cm² was observed at 28 cd/A, and a life span to theluminance of 90% was 300 hours.

EXPERIMENTAL EXAMPLE 2

The same process was performed to manufacture an organic EL device,except that the compound of Formula 3 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.7 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.31, 0.64) at a current density of 50mA/cm² was observed at 30 cd/A, and a life span to the luminance of 90%was 310 hours.

EXPERIMENTAL EXAMPLE 3

The same process was performed to manufacture an organic EL device,except that the compound of Formula 4 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.5 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.32, 0.65) at a current density of 50mA/cm² was observed at 29 cd/A, and a life span to the luminance of 90%was 340 hours.

EXPERIMENTAL EXAMPLE 4

The same process was performed to manufacture an organic EL device,except that the compound of Formula 7 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.6 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.31, 0.65) at a current density of 50mA/cm² was observed at 29 cd/A, and a life span to the luminance of 90%was 320 hours.

EXPERIMENTAL EXAMPLE 5

The same process was performed to manufacture an organic EL device,except that the compound of Formula 13 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.7 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.32, 0.64) at a current density of 50mA/cm² was observed at 30 cd/A, and a life span to the luminance of 90%was 350 hours.

EXPERIMENTAL EXAMPLE 6

The same process was performed to manufacture an organic EL device,except that the compound of Formula 17 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.6 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.31, 0.65) at a current density of 50mA/cm² was observed at 29 cd/A, and a life span to the luminance of 90%was 330 hours.

EXPERIMENTAL EXAMPLE 7

The same process was performed to manufacture an organic EL device,except that the compound of Formula 22 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.5 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.32, 0.65) at a current density of 50mA/cm² was observed at 29 cd/A, and a life span to the luminance of 90%was 370 hours.

EXPERIMENTAL EXAMPLE 8

The same process was performed to manufacture an organic EL device,except that the compound of Formula 27 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.6 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.32, 0.64) at a current density of 50mA/cm² was observed at 29 cd/A, and a life span to the luminance of 90%was 360 hours.

EXPERIMENTAL EXAMPLE 9

The same process was performed to manufacture an organic EL device,except that the compound of Formula 32 was used instead of the compoundof Formula 2 in Experimental Example 1.

A forward current density of 4.7 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.32, 0.65) at a current density of 50mA/cm² was observed at 30 cd/A, and a life span to the luminance of 90%was 390 hours.

COMPARATIVE EXAMPLE 1

The same process was performed to manufacture an organic EL device,except that 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) of thefollowing Formula was used instead of the compound of Formula 2 inExperimental Example 1.

A forward current density of 4.5 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.32, 0.64) at a current density of 50mA/cm² was observed at 27 cd/A, and a life span to the luminance of 90%was 140 hours.

COMPARATIVE EXAMPLE 2

The same process was performed to manufacture an organic EL device,except that the compound of the following Formula HT1 was used insteadof the compound of Formula 2 in Experimental Example 1.

A forward current density of 4.6 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.31, 0.64) at a current density of 50mA/cm² was observed at 28 cd/A, and a life span to the luminance of 90%was 250 hours.

COMPARATIVE EXAMPLE 3

The same process was performed to manufacture an organic EL device,except that the compound of the following Formula HT2 was used insteadof the compound of Formula 2 in Experimental Example 1.

A forward current density of 4.7 V was applied to the light emittingdevice manufactured in the above, and as a result, the green light inwhich the color coordinate was (0.32, 0.65) at a current density of 50mA/cm² was observed at 29 cd/A, and a life span to the luminance of 90%was 270 hours.

INDUSTRIAL APPLICABILITY

The compound of the present invention is used in an organic lightemitting device, and the organic light emitting device that includes thecompound as an organic material layer largely improves life span,efficiency, electrochemical stability, and thermal stability.

1. A compound of Formula 1:

wherein X is selected from the group consisting of hydrogen; an alkylgroup, which is substituted or unsubstituted with one or moresubstituent groups selected from the group consisting of a halogengroup, an alkyl group, an alkenyl group, an alkoxy group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted arylalkylgroup, a substituted or unsubstituted arylalkenyl group, a substitutedor unsubstituted hetero ring group, a substituted or unsubstitutedcarbazolyl group, a substituted or unsubstituted fluorenyl group, anitrile group and an acetylene group; an alkoxy group, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkenyl group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an aryl group, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an hetero ring group including O, N or S as aheteroatom, which is substituted or unsubstituted with one or moresubstituent groups selected from the group consisting of a halogengroup, an alkyl group, an alkenyl group, an alkoxy group, a substitutedor unsubstituted aryl amine group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group! a carbazolyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorernyl group, a nitrile group and anacetylene group; —N(R′)(R″); a nitrile group; anitro group; a halogengroup; —CO—N(R′)(R″); and —COO—R′, R′ and R″ are each independentlyselected from the group consisting of hydrogen, a halogen group, analkyl group, an alkenyl group, an alkoxy group, a substituted orunsubstituted aryl group, a substituted or unsubstituted arylalkylgroup, a substituted or unsubstituted aryl alkenyl group, a substitutedor unsubstituted hetero ring group, a substituted or unsubstitutedcarbazolyl group, a substituted or unsubstituted fluorenyl group, anitrile group and an acetylene group, L is an arylene group, which issubstituted or unsubstituted with one or more substituent groupsselected from the group consisting of nitro, nitrile, halogen, an alkylgroup, an alkoxy group and an amino group and has 6 to 40 carbon atoms!a divalent hetero ring group, which is substituted or unsubstituted withone or more substituent groups selected from the group consisting ofnitro, nitrile, halogen, an alkyl group, an alkoxy group and an aminogroup; or a fluoarenylene group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof nitro, nitrile, halogen, an alkyl group, an alkoxy group and an aminogroup, R₁ and R₂ are each independently selected from the groupconsisting of hydrogen; deuterium; an alkyl group, which is substitutedor unsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group! an alkoxy group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group! an alkenyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an aryl group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedaryl alkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an hetero ring groupincluding O, N or S as a heteroatom, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an aikoxy group, a substituted or unsubstituted arylamine group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolvi group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; a carbazolyl group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted unsubstituted fluorenyl group, a nitrile group and anacetylene group; a fluorenyl group, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an aryloxy group, which is substituted or unsubstitutedwith one or more substituent groups selected from the group consistingof a halogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; an arylthio group, whichis substituted or unsubstituted with one or more substituent groupsselected from the group consisting of a halogen group, an alkyl group,an alkenyl group, an alkoxy group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; an alkoxycarbonyl group, which is substitutedunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted aryl group, asubstituted or unsubstituted arylalkyl group, a substituted orunsubstituted arylalkenyl group, a substituted or unsubstituted heteroring group, a substituted or unsubstituted carbazolyl group,asubstituted or unsubstituted fluorenyl group, a nitrile group and anacetylene group; a hydroxyl group; a carboxyl group; a nitrile group; anitro group; a halogen group; —N(R′)(R″); a nitrile group; anitro group;a halogen group; —CO—N(R′)(R″); and —COO—R′, and said R₁ and R₂ may forman aliphatic or hetero condensation ring in conjunction with adjacentgroups, and at least one of R₃ to R₉ is deuterium, and the remains of R₃to R₉ are hydrogen.
 2. The compound as set forth in claim 1, wherein Xof Formula 1 selected from the group consisting of a phenyl group, abiphenyl group, a terphenyl group, a stilbene group, anaphthyl group, ananthracenyl group, a phenanthrene group, a pyrenyl group, a perylenylgroup, a carhazolyl group, a fluorenyl group, a thiophene group, a furangroup, a pyrrolyl group, an imidazolyl group, a thiazolyl group, anoxazolyl group, an oxadiazolyl group, atriazolyl group, apyridyl group,a pyradazine group, a quinolinyl group, an isoquinoline group, and anacridyl group.
 3. The compound as set forth in claim 1, wherein L is aphenylene group, which is substituted or unsubstituted by one or moresubstituent groups selected from the group consisting of nitro, nitrile,halogen, an alkyl group, an alkoxy group and an amino group; a divalenthetero ring group including O, N or S and 5 or 6 carbon atoms, which issubstituted or unsubstituted by one or more substituent groups selectedfrom the group consisting of nitro, nitrile, halogen, an alkyl group, analkoxy group and an amino group! or a fluorenylene group, which issubstituted or unsubstituted by one or more substituent groups selectedfrom the group consisting of nitro, nitrile, halogen, an alkyl group, analkoxy group and an amino group.
 4. The compound as set forth in claiml, wherein L is a phenylene group or a fluorenylene group.
 5. Thecompound as set forth in claim 1, wherein R₁ and R₂ are eachindependently an aryl group, which is substituted or unsubstituted withone or more substituent groups selected from the group consisting of ahalogen group, an alkyl group, an alkenyl group, an alkoxy group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carhazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group; or an hetero ring groupincluding O, N or S as aheteroatom, which is substituted orunsubstituted with one or more substituent groups selected from thegroup consisting of a halogen group, an alkyl group, an alkenyl group,an alkoxy group, a substituted or unsubstituted arylamine group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylalkyl group, a substituted or unsubstituted arylalkenyl group, asubstituted or unsubstituted hetero ring group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted fluorenylgroup, a nitrile group and an acetylene group.
 6. The compound as setforth in claim 1, wherein R₁ and R₂ are each independently any one ofthe following groups:


7. An organic light emitting device that includes a first electrode, anorganic material layer that includes one or more layers having a lightemitting layer, and a second electrode sequentially layered, wherein theorganic light emitting device comprises one or more layers of theorganic material layer that include the compound of Formula 1 of claim1, or the compound of Formula 1 into which a thermosetting group or aphotocurable functional group is introduced.
 8. The organic lightemitting device as set forth in claim 7 wherein the organic materiallayer includes a hole transport layer, and the hole transport layerincludes the compound of Formula 1 or the compound of Formula 1 intowhich a thermosetting group or a photocurable functional group isintroduced.
 9. The organic light emitting device as set forth in claim7, wherein the organic material layer includes a hole injection layer,and the hole injection layer includes the compound of Formula 1 or thecompound of Formula 1 into which a thermosetting group or a photocurablefunctional group is introduced.
 10. The organic light emitting device asset forth in claim 7, wherein the organic material layer includes alayer that collectively inject and transport a hole, and the layerincludes the compound of Formula 1 or the compound of Formula 1 intowhich a thermosetting group or a photocurable functional group isintroduced.
 11. The organic light emitting device as set forth in claim7, wherein the organic material layer includes an electron injection andtransport layer, and the electron injection and transport layer includesthe compound of Formula 1 or the compound of Formula 1 into which athermosetting group or a photocurable functional group is introduced.12. The organic light emitting device as set forth in claim 7, whereinthe light emitting layer includes the compound of Formula 1 or thecompound of Formula 1 into which a thermosetting group or a photocurablefunctional group is introduced.